HCID 71295661, compound → HCID 71295500, compound

Participants

Reaction Steps

DMP (742 mg, 1.749 mmol) was added to the solution of 2-bromo-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-ol (500 mg, 1.46 mmol) in CH2Cl2 (5 mL) at 0° C. The mixture was stirred at room temperature overnight. The mixture was then diluted with saturated Na2S2O3 and NaHCO3 (30 mL, 30 mL). The mixture was extracted with ethyl acetate (20 mL×3). The organic layer was washed with brine (30 mL×3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EA=3:1) to provide 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (350 mg, yield: 70.4%). 1H-NMR (CDCl3, 400 MHz) δ 7.55˜7.68 (m, 2H), 7.53 (t, J=6.0 Hz, 1H), 7.35˜7.37 (m, 1H), 7.28˜7.30 (m, 1H), 7.17˜7.24 (m, 1H), 7.08 (t, J=8.4 Hz, 1H), 6.70 (d, J=0.8 Hz, 1H), 4.73 (s, 2H), 4.55 (s, 2H). MS (M+H)+: 342/344.

Provenance & Evidence